関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Ethyl formate | HCID 8025 | — |
| 反応物 | Sodium Methoxide | HCID 10942334 | — |
| 反応物 | 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone | HCID 22667147 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | HCID 178486758 | HCID 178486758 | 72.4% |
反応手順
To a solution of 1-(2-Amino-4-benzyloxy-5-methoxy-phenyl)-ethanone (108 mmol, 29.3 g) in DME (700 ml) was added sodium methoxide (432 mmol, 23.35 g). The mixture was stirred for 30 minutes. Ethyl formate (540 mmol, 44 ml) was added and the mixture was stirred overnight. (Additional sodium methoxide may be needed if reaction is not complete as monitored by LC/MS.) After the reaction was completion, the mixture was diluted with water (40 ml) and acidified to neutral with 1M HCl. The precipitate was filtered and washed with water, dried in vacuo to afford 22 g (72%) of 7-benzyloxy-6-methoxy-quinolin-4-ol. 1H NMR (CDCl3): 10.7 (1H, br), 7.703 (1H, s), 7.493-7.461 (1H, t), 7.431-7.413 (2H, br d), 7.372-7.333 (2H, t), 7.296-7.283 (1H, d), 6.839 (1H, s), 6.212-6.193 (1H, d), 5.212 (2H, s), 3.965 (3H, s). LC/MS (M+1=282).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08476298B2 |
|---|
| 出典データセット | uspto-grants-2013_07 |
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| ORD ID | ord-beb0ffcb1cf9429891731164fd82ee4d |
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| 出典メモ | uspto-grants-2013_07 |
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